Bicyclo[2.2.1]heptane, 7,7-dimethyl-2-methylene-

Formula: C₁₀H₁₆
Molecular weight: 136.2340
IUPAC Standard InChI: InChI=1S/C10H16/c1-7-6-8-4-5-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3
IUPAC Standard InChIKey: XCPQUQHBVVXMRQ-UHFFFAOYSA-N
CAS Registry Number: 471-84-1
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: Norbornane, 7,7-dimethyl-2-methylene-; α-Fenchene; Fenchene; 7,7-Dimethyl-2-methylenenorbornane; 7,7-Dimethyl-2-methylen-bicyclo(2,2,1)heptane; 7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane; Fenchene, Bicyclo[2.2.1]heptane,2-methylene 5,5-dimethyl-
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Normal alkane RI, non-polar column, temperature ramp

Go To: Top, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SPB-1	SLB-5 MS	DB-5	SPB-5	5 % Phenyl methyl siloxane
Column length (m)	30.	10.	30.	30.	60.
Carrier gas	Helium	Helium	Helium	Nitrogen	Helium
Substrate
Column diameter (mm)	0.20	0.10	0.25	0.53	0.25
Phase thickness (μm)	0.20	0.10	0.25	0.50	0.25
T_start (C)	70.	50.	35.	50.	90.
T_end (C)	220.	250.	220.	210.	225.
Heat rate (K/min)	3.	10.	3.	3.	3.
Initial hold (min)				5.
Final hold (min)	15.		40.	45.	3.
I	943.	947.	951.	938.	951.
Reference	Neves, Rosa, et al., 2010	Scandinaro, Tranchida, et al., 2010	El-Massry, El-Ghorab, et al., 2009	Gilani, Shah, et al., 2009	Retta, Gattuso, et al., 2009
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	HP-5 MS	HP-5	DB-5	SPB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	Nitrogen	Helium	N2	Helium	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	40.	50.	50.	60.	50.
T_end (C)	230.	230.	240.	300.	250.
Heat rate (K/min)	2.	3.	5.	3.	2.
Initial hold (min)		10.	1.
Final hold (min)		10.	4.
I	953.	953.	953.	925.	944.
Reference	Scrivanti, Anton, et al., 2009	Adams, Beauchamp, et al., 2007	Cheraif, Ben Jannet, et al., 2007	Moreno, Lima, et al., 2007	Raal, Orav, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	HP-5MS	HP-5	HP-5	AT-5
Column length (m)	30.	30.	30.	30.	60.
Carrier gas	He	He	N2	N2	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	40.	40.	50.	50.	60.
T_end (C)	250.	260.	280.	280.	200.
Heat rate (K/min)	3.	4.	9.	9.	4.
Initial hold (min)	5.		3.	3.
Final hold (min)	10.		3.	3.	20.
I	939.	940.9	944.	949.	946.
Reference	Vichi, Riu-Aumatell, et al., 2007	Zizovic, Stamenic, et al., 2007	Abdelwahed, Hayder, et al., 2006	Abdelwahed, Hayder, et al., 2006	Borges, Rojas, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SPB-1	HP-5 MS	HP-5	HP-5	CP Sil 5 CB
Column length (m)	30.	30.	30.	25.	25.
Carrier gas	Helium	Nitrogen	N2	N2
Substrate
Column diameter (mm)	0.20	0.25	0.25	0.2	0.25
Phase thickness (μm)	0.20	0.25	0.52	0.33	0.15
T_start (C)	70.	50.	50.	30.	50.
T_end (C)	220.	280.	280.	280.	230.
Heat rate (K/min)	3.	5.	5.	3.	3.
Initial hold (min)
Final hold (min)	15.	5.	5.
I	943.	950.	950.	951.	947.
Reference	Cavaleiro, Pinto, et al., 2006	Marzouk, Mansour, et al., 2006	Marzouk, Neffati, et al., 2006	Shafi, Jose, et al., 2006	Ogunwande, Olawore, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	DB-1	DB-5HT	HP-5MS	RSL-200
Column length (m)	30.	50.	27.	30.	30.
Carrier gas		He	He	He	H2
Substrate
Column diameter (mm)	0.2	0.22	0.25	0.25	0.32
Phase thickness (μm)		0.25		0.25	0.25
T_start (C)	60.	70.	50.	60.	40.
T_end (C)	280.	220.	250.	275.	280.
Heat rate (K/min)	3.	4.	2.	4.	6.
Initial hold (min)			2.		5.
Final hold (min)			20.		5.
I	953.	950.	951.	948.	943.
Reference	Petrakis, Roussis, et al., 2005	Palá-Paúl, García-Jiménez, et al., 2004	Yusufoglu, Celik, et al., 2004	Hajhashemi, Ghannadi, et al., 2003	Jirovetz, Buchbauer, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	HP-5	HP-5	HP-1	5 % Phenyl methyl siloxane
Column length (m)	50.	30.	60.	30.	30.
Carrier gas	He	He		He	He
Substrate
Column diameter (mm)	0.2	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	50.	60.	40.	70.	75.
T_end (C)	220.	280.	250.	220.	200.
Heat rate (K/min)	3.	3.	5.	3.	3.
Initial hold (min)	2.		15.		4.
Final hold (min)				15.	8.
I	947.	924.	951.	941.	953.
Reference	Masotti, Juteau, et al., 2003	Pitarokili, Tzakou, et al., 2003	Stashenko, Jaramillo, et al., 2003	Cavaleiro, Salgueiro, et al., 2002	Cicció and Gómez-Laurito, 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-1	SPB-1	BP-1	DB-5
Column length (m)	30.	50.	30.	25.	30.
Carrier gas	He	N2	He	N2
Substrate
Column diameter (mm)	0.25	0.25	0.2	0.33	0.32
Phase thickness (μm)	0.25	0.25	0.2	1.0	1.
T_start (C)	60.	60.	80.	60.	40.
T_end (C)	300.	240.	300.	275.	200.
Heat rate (K/min)	2.	3.	5.	4.	3.
Initial hold (min)			3.		5.
Final hold (min)
I	950.	937.	952.	950.	961.
Reference	Ruberto, Biondi, et al., 2002	Velasco-Negueruela, Pérez-Alonso, et al., 2002	Fraternale, Giamperi, et al., 2000	Mohagheghzadeh, Shams-Ardakani, et al., 2000	Meynier, Novelli, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary
Active phase	SPB-5	CP Sil 5 CB	SPB-Sulfur	SE-54
Column length (m)	50.	25.	30.	30.
Carrier gas	He	He	He	Hydrogen
Substrate
Column diameter (mm)	0.32	0.25	0.32	0.25
Phase thickness (μm)	0.25	0.25	4.	0.25
T_start (C)	60.	60.	45.	60.
T_end (C)	240.	300.	240.	250.
Heat rate (K/min)	3.	6.	5.	2.
Initial hold (min)			13.	5.
Final hold (min)	20.		5.	2.
I	949.	930.	959.	945.
Reference	Doneanu and Anitescu, 1998	Bos, Woerdenbag, et al., 1997	Mariaca, Berger, et al., 1997	Kollmannsberger, Nitz, et al., 1992
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, Notes

Neves, Rosa, et al., 2010
Neves, A.; Rosa, S.; Goncalves, J.; Rufino, A.; Judas, F.; Salgueiro, L.; Lopes, M.C.; Cavaleiro, C.; Mendes, A.F., Screening of five essential oils for identification of potential inhibitors of IL-1-unduced Nf-kB activation and NO production in human clondrocytes: characterization of the inhibitory activity of alpha-pinene, Plante Med., 2010, 76, 03, 303-308, https://doi.org/10.1055/s-0029-1186085 . [all data]

Scandinaro, Tranchida, et al., 2010
Scandinaro, M.; Tranchida, P.Q.; Costa, R.; Dugo, P.; Mondello, L., Rapid Quality Control of Flavours and Fragrances using Fast GC-MS and Multi-MS Library Search Procedures, LCGC Europe, 2010, 23, 9, 456-464. [all data]

El-Massry, El-Ghorab, et al., 2009
El-Massry, K.F.; El-Ghorab, A.H.; Shaaban, H.A.; Shibamoto, T., Chemical compositions and antioxidant/antimicrobial activities of various samples prepared from Schinus terebinthifolius leaves cultivated in Egipt, J. Agric. Food Chem., 2009, 57, 12, 5265-5270, https://doi.org/10.1021/jf900638c . [all data]

Gilani, Shah, et al., 2009
Gilani, A.H.; Shah, A.J.; Zubair, A.; Khalid, S.; Kiani, J.; Ahmed, A.; Rasheed, M.; Ahmad, V.U., Chemical composition and mechanisms underlying the spasmolytic and bronchodilatory properties of the essential oil of Nepeta cataria L., J. Ethnopharmacology, 2009, 121, 3, 405-411, https://doi.org/10.1016/j.jep.2008.11.004 . [all data]

Retta, Gattuso, et al., 2009
Retta, D.; Gattuso, M.; Gattuso, S.; Lira, P. Di Leo; van Baren, C.; Ferraro, G.; Bandoni A., Essential oil composition of Achyrocline flaccida (Weinm.) DC. (Asteraceae) from different locations of Argentina, Biochem. Systematics Ecol., 2009, 36, 12, 877-881, https://doi.org/10.1016/j.bse.2008.11.001 . [all data]

Scrivanti, Anton, et al., 2009
Scrivanti, L.R.; Anton, A.M.; Zygadlo, J.A., Essential oil conposition of Bothriochloa Kuntze (Poaceae) from South America and their chemotaxonomy, Biochem. Systematics Ecol., 2009, 37, 3, 206-213, https://doi.org/10.1016/j.bse.2009.03.009 . [all data]

Adams, Beauchamp, et al., 2007
Adams, R.P.; Beauchamp, P.S.; Dev, V.; Dutz, S.M., New Natural Products Isolated from One-Seeded Juniperus of the Southwestern United States: Isolation and Occurence of 2-Ethenyl-3-methyl Phanol and Its Derivatives, J. Essent. Oil Res., 2007, 19, 2, 146-152, https://doi.org/10.1080/10412905.2007.9699247 . [all data]

Cheraif, Ben Jannet, et al., 2007
Cheraif, I.; Ben Jannet, H.; Hammami, M.; Khouja, M.L.; Mighri, Z., Chemical composition and antimicrobial activity of essential oils of Cupressus arizonica Greene, Biochem. Syst. Ecol., 2007, 35, 12, 813-820, https://doi.org/10.1016/j.bse.2007.05.009 . [all data]

Moreno, Lima, et al., 2007
Moreno, P.R.H.; Lima, M.E.L.; Sobral, M.; Young, M.C.M.; Cordeiro, I.; Apel, M.A.A.; Limberger, R.P.; Henriques, A.T., Essential oil composition of fruit colour varieties of Eugenia brasiliensis Lam., Sci. Agr.; (Piracicaba Praz.), 2007, 64, 4, 428-432. [all data]

Raal, Orav, et al., 2007
Raal, A.; Orav, A.; Arak, E.; Kailas, T.; Müürisepp, M., Variation in the composition of the essential oil of Valeriana officinalis L. roots from Estonia, Proc. Est. Acad. Sci. Chem., 2007, 56, 2, 67-74. [all data]

Vichi, Riu-Aumatell, et al., 2007
Vichi, S.; Riu-Aumatell, M.; Mora-Pons, M.; Guadayol, J.M.; Buxaderas, S.; López-Tamames, E., Analytical, Nutritional and Clinical Methods. HS-SPME coupled to GC/MS for quality control of Juniperus communis L. berries used for gin aromatization, Food Chem., 2007, 105, 4, 1748-1754, https://doi.org/10.1016/j.foodchem.2007.03.026 . [all data]

Zizovic, Stamenic, et al., 2007
Zizovic, I.; Stamenic, M.; Ivanovic, J.; Orlovic, A.; Ristic, M.; Djordjevic, S.; Petrovic, S.D.; Skala, D., Supercritical carbon dioxide extraction of sesquiterpenes from valerian root, J. Supercrit. Fluids, 2007, 43, 2, 249-258, https://doi.org/10.1016/j.supflu.2007.05.007 . [all data]

Abdelwahed, Hayder, et al., 2006
Abdelwahed, A.; Hayder, N.; Kilani, S.; Mahmoud, A.; Chibani, J.; Hammami, M.; Chekir-Ghedira, L.; Ghedira, K., Chemical composition and antimicrobial activity of essential oils from Tunisian Pituranthos tortuosus (Coss.) Maire, Flavour Fragr. J., 2006, 21, 1, 129-133, https://doi.org/10.1002/ffj.1542 . [all data]

Borges, Rojas, et al., 2006
Borges, R.; Rojas, L.B.; Cegarra, J.A.; Usubillaga, A., Study of the essential oils from the leaves and flowers of Lepechinia conferta (Benth) Epl., Flavour Fragr. J., 2006, 21, 1, 155-157, https://doi.org/10.1002/ffj.1550 . [all data]

Cavaleiro, Pinto, et al., 2006
Cavaleiro, C.; Pinto, E.; Gonsales, M.J.; Salguero, L., Antifungal activity of Juniperus essential oils agains dermatophyte, Asrgillus and Candida strains, J. Appl. Microbiol., 2006, 100, 6, 1333-1338, https://doi.org/10.1111/j.1365-2672.2006.02862.x . [all data]

Marzouk, Mansour, et al., 2006
Marzouk, Z.; Mansour, H.B.; Chraief, I.; Mosrati, R.; Cheriaa, J.; Neffati, A.; Marzouk, B.; Sfari, M.; Boukef, K.; Barillies, D.; Ghedira, L.C., Chemical composition, antibacterial and antimutagenic activities of four populations of Rosmarinus officinalis L. oils from Tunisia, J. Food Agriculture Environment, 2006, 4, 2, 89-94. [all data]

Marzouk, Neffati, et al., 2006
Marzouk, Z.; Neffati, A.; Marzouk, B.; Chraief, I.; Fathia, K.; Ghedira, L.C.; Boukef, K., Chemical composition and antibacterial and antimutagenic activity of Tunisian Rosmarinus officinalis L. oil from Kasrine, Journal of Food, Agriculture Environment, 2006, 4, 34, 61-65. [all data]

Shafi, Jose, et al., 2006
Shafi, P.M.; Jose, B.; Radhamani, K.T.; Clery, R.A., Influence of pH on essential oil composition of Zanthoxylum rhetsa seeds obtained by steam distillation, Flavour Fragr. J., 2006, 21, 2, 317-318, https://doi.org/10.1002/ffj.1598 . [all data]

Ogunwande, Olawore, et al., 2005
Ogunwande, I.A.; Olawore, N.O.; Adeleke, K.A.; Ekundayo, O., Volatile constituents from the leaves of Eucalyptus cloeziana F. Muell and E. propinqua Deane Maiden from Nigeria, Flavour Fragr. J., 2005, 20, 6, 637-639, https://doi.org/10.1002/ffj.1516 . [all data]

Petrakis, Roussis, et al., 2005
Petrakis, P.V.; Roussis, V.; Papadimitriou, D.; Vagias, C.; Tsitsimpikou, C., The effect of terpenoid extracts from 15 pine species on the feeding behavioural sequence of the late instars of the pine processionary caterpillar Thaumetopoea pityocampa, Behav. Processes, 2005, 69, 3, 303-322, https://doi.org/10.1016/j.beproc.2004.12.008 . [all data]

Palá-Paúl, García-Jiménez, et al., 2004
Palá-Paúl, J.; García-Jiménez, R.; Pérez-Alonso, M.J.; Velasco-Negueruela, A.; Sanz, J., Essential oil composition of the leaves and stems of Meum athamanticum Jacq., from Spain, J. Chromatogr. A, 2004, 1036, 2, 245-247, https://doi.org/10.1016/j.chroma.2004.02.064 . [all data]

Yusufoglu, Celik, et al., 2004
Yusufoglu, A.; Celik, H.; Kirbaslar, G., Utilization of Lavandula angustifolia Miller extracts as natural repellents, pharmaceutical and industrial auxiliaries, J. Serb. Chem. Soc., 2004, 69, 1, 1-7, https://doi.org/10.2298/JSC0401001Y . [all data]

Hajhashemi, Ghannadi, et al., 2003
Hajhashemi, V.; Ghannadi, A.; Sharif, B., Anti-inflammatory and analgesic properties of the leaf extracts and essential oil of Lavandula angustifolia Mill., J. Ethnopharmacol., 2003, 89, 1, 67-71, https://doi.org/10.1016/S0378-8741(03)00234-4 . [all data]

Jirovetz, Buchbauer, et al., 2003
Jirovetz, L.; Buchbauer, G.; Shafi, M.P.; Leela, N.K., Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India, Acta Pharm. Hung., 2003, 53, 73-81. [all data]

Masotti, Juteau, et al., 2003
Masotti, V.; Juteau, F.; Bessière, J.M.; Viano, J., Seasonal and phenological variations of the essential oil from the narrow endemic species Artemisia molinieri and its biological activities, J. Agric. Food Chem., 2003, 51, 24, 7115-7121, https://doi.org/10.1021/jf034621y . [all data]

Pitarokili, Tzakou, et al., 2003
Pitarokili, D.; Tzakou, O.; Loukis, A.; Harvala, C., Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens, J. Agric. Food Chem., 2003, 51, 11, 3294-3301, https://doi.org/10.1021/jf0211534 . [all data]

Stashenko, Jaramillo, et al., 2003
Stashenko, E.E.; Jaramillo, B.E.; Martínez, J.R., Comparación de la composición química y de la actividad antioxidante in vitro de los metabolitos secundarios volátiles de plantas de la familia verbenaceae, Rev. Acad. Colomb. Cienc. Exactas Fis. Nat., 2003, 27, 105, 579-597. [all data]

Cavaleiro, Salgueiro, et al., 2002
Cavaleiro, C.; Salgueiro, L.; Barroso, J.G.; Figueiredo, A.C.; Pedro, L.G.; Fontinha, S.S.; Bighelli, A.; Casanova, J.; Looman, A.; Scheffer, J.J.C., Composition of the essential oil of Juniperus cedrus Webb and Berth. grown on Madeira, Flavour Fragr. J., 2002, 17, 2, 111-114, https://doi.org/10.1002/ffj.1061 . [all data]

Cicció and Gómez-Laurito, 2002
Cicció, J.F.; Gómez-Laurito, J., Volatile constituents of the leaves of Siparuna thecaphora (Siparunaceae) from Turrialba, Costa Rica, Rev. Biol. Trop., 2002, 50, 3/4, 963-967. [all data]

Ruberto, Biondi, et al., 2002
Ruberto, G.; Biondi, D.; Barbagallo, C.; Meli, R.; Savoca, F., Constituents of stem and flower oils of Helichrysum litoreum Guss., Flavour Fragr. J., 2002, 17, 1, 46-48, https://doi.org/10.1002/ffj.1037 . [all data]

Velasco-Negueruela, Pérez-Alonso, et al., 2002
Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Palá-Paúl, J.; Íñigo, A.; López, G., Leaf essential oils analysis of Juniperus navicularis Gandoger, Botanica Complutensis, 2002, 26, 85-91. [all data]

Fraternale, Giamperi, et al., 2000
Fraternale, D.; Giamperi, L.; Ricci, D.; Manunta, A., Composition of the essential oil of Peucedanum verticillare, Biochem. Syst. Ecol., 2000, 28, 2, 143-147, https://doi.org/10.1016/S0305-1978(99)00049-6 . [all data]

Mohagheghzadeh, Shams-Ardakani, et al., 2000
Mohagheghzadeh, A.; Shams-Ardakani, M.; Ghannadi, A., Linalol-rich essential oil of Zataria multiflora Boiss. (Lamiaceae), Flavour Fragr. J., 2000, 15, 2, 119-122, https://doi.org/10.1002/(SICI)1099-1026(200003/04)15:2<119::AID-FFJ878>3.0.CO;2-V . [all data]

Meynier, Novelli, et al., 1999
Meynier, A.; Novelli, E.; Chissolinim, R.; Zanardi, E.; Gandemer, G., Volatile compounds of commercial Milano salami, Meat Sci., 1999, 51, 2, 175-183, https://doi.org/10.1016/S0309-1740(98)00122-3 . [all data]

Doneanu and Anitescu, 1998
Doneanu, C.; Anitescu, G., Supercritical carbon dioxide extraction of Angelica archangelica L. root oil, J. Supercrit. Fluids, 1998, 12, 1, 59-67, https://doi.org/10.1016/S0896-8446(97)00040-5 . [all data]

Bos, Woerdenbag, et al., 1997
Bos, R.; Woerdenbag, H.J.; Hendriks, H.; Scheffer, J.J.C., Composition of the essential oils from underground parts of Valeriana officinalis L. s.l. and several closely related taxa, Flavour Fragr. J., 1997, 12, 5, 359-370, https://doi.org/10.1002/(SICI)1099-1026(199709/10)12:5<359::AID-FFJ660>3.0.CO;2-G . [all data]

Mariaca, Berger, et al., 1997
Mariaca, R.G.; Berger, T.F.H.; Gauch, R.; Imhof, M.I.; Jeangros, B.; Bosset, J.O., Occurrence of volatile mono- and sesquiterpenoids in highland and lowland plant species as possible precursors for flavor compounds in milk and dairy products, J. Agric. Food Chem., 1997, 45, 11, 4423-4434, https://doi.org/10.1021/jf970216t . [all data]

Kollmannsberger, Nitz, et al., 1992
Kollmannsberger, H.; Nitz, S.; Drawert, F., UBer die Aromastoffzusammensetzung von Hochdruckextrakten. I. Pfeffer (Piper nigrum, Var. muntok), Z. Lebensm. Unters Forsch., 1992, 194, 6, 545-551, https://doi.org/10.1007/BF01185481 . [all data]

Notes

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, References

Symbols used in this document:

T_end Final temperature

T_start Initial temperature
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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